


It’s Love, Stupid

by Starkangejr



Category: Green Arrow (Comics)
Genre: Crossdressing, Dead Dove: Do Not Eat, Fluff, Lingerie, M/M, Size Difference, Underage Drinking, Undercover
Language: English
Status: In-Progress
Published: 2019-12-26
Updated: 2019-12-26
Packaged: 2021-02-26 07:07:48
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 3,431
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21959365
Author URL: https://archiveofourown.org/users/Starkangejr/pseuds/Starkangejr
Summary: Based on prompts for a Gift Exchange—Roy dresses up for a mission and catches some feelings.
Relationships: Roy Harper/Oliver Queen
Comments: 8
Kudos: 38





	It’s Love, Stupid

**Author's Note:**

> If this is not your cup of tea, please leave. I’ve tagged everything for you to know what’s up.
> 
> I’ve left Roy’s age to be ambiguous, hence the underaged tag. He’s young but who’s to say how young. That’s up to you! I hope you enjoy this gift I created for the gift exchange!

Roy scratches at his scalp for the millionth time in the last minute. He drops his hand immediately the second Ollie turns towards him. He's as still as a doll while the old man dabs at his face with a soft sponge, the wig cap on Roy’s head cutting off some blood circulation to his poor brain—that’s what it feels like—as he plays nice, sits and behaves like a good sidekick. He’s a good boy. Roy reasons all this torture is all for the better since dressing up seems the only way that'll sell their story perfectly. They're going undercover—usually the type of job left to Robin and Batman—but Star City is their turf and Ollie hates letting The Bat have one leg up on him. His competitive streak is passed on to Roy and this is just one of those things where the kid has to grin and bear it. The makeup doesn’t take long to transform his face. The fake lashes he struggled an hour putting on earlier are paying off now when Ollie sits back and whistles. Roy peaks at his mentor, staring into the mirror and admiring his transformation. The lipstick is a shock of bright red, complemented by the dark eyeshadow and eyeliner making Roy feel like he is actually looking at someone else. The lack of hair throws him off though and he watches Ollie come back with the wig of dirty blond hair ready to pull it over his head. 

“Why do you have this stuff again?” He can’t help himself from blurting out as he fights the pull of the wig while Ollie sets it in place. Roy’s head rocks back and forth with the strain of fighting gravity and finally the damn thing stops moving. Ollie tugs on a strand, snickering at Roy as he catches his eyes in the mirror.

“I told you, I bought it online. Now hold still, your bangs are off center.” Ollie is too focused on making the wig look like real hair and Roy squirms in the chair, tired of sitting for so long.

“I bet Bruce doesn’t have Dick change his hair.” He mumbles under his breath with a slight pout to his lip. This cap will squeeze his scalp clean off. Roy’s certain of it.

“That’s because boy wonder has a head of hair that doesn’t fight _against_ hair products.” Ollie snides, giving his sidekick a pointed glare.

“Hey, it’s not my fault you bought cheap-o brushes and hairspray!” Roy defends himself, tossing his arms in the air and trying to bat Ollie’s hands away.

“They were not cheap, Roy, your hair just can’t be contained. So wig we go. You have to look the part. You should be glad I’m even bringing you.” Ollie sighs, giving up when Roy turns around and crosses his arms over his chest. Sometimes, being a mentor feels like a mistake. But Ollie knows all the secret words that'll get Roy to obey. Ollie shrugs his shoulders, nonchalant as he steps away.

“You know, Hal is just a phone call away,” he starts, heading for the phone by the hallway, not even bothering giving the kid a backwards glance.

“No!” Roy shouts, standing to his feet as he looks for the package with his outfit and races towards it. “I can do it. We don’t need him.” He huffs, defiant as he grabs the costume and rushes to change.

Ollie snickers to himself, watching Roy go. “Works every time.”

* * *

Roy tears into the package, letting the contents fall over the bed with little attention. He gets the basic idea of how to put on the dress after unzipping the frilly thing open to reveal its inner workings. What confuses him is the extra garments. Is he supposed to wear all of this underneath the dress? The first fabric is soft to the touch and the identity of the underwear isn’t lost on the young hero. Ollie said he’d bought this stuff online for Roy to wear, but in reality the old man probably just clicked Buy on the first thing that popped up on the search. There’s no way Ollie knew this was in here...right?

 _Definitely doesn’t, he would have tried to hide this shit from me. It’ll just help me get into character, if nothing else,_ Roy reasons to himself as he slips the soft cottoned panties on, followed by the white stockings that try to squeeze the air out of his gut. Roy wheezes, adjusting the line of the stockings before looking down at the bed at the last piece of clothing. _It’s a little unnecessary,_ he thinks, staring down at the laced bralette. It mocks him as it lays there, goading him to stomp out of the room in a flurry of biting words and anger at Ollie. But Roy reminds himself how much he begged to help on this mission. He needs to commit, go all the way, otherwise Ollie will just leave him like always, doing whatever it is he does when Hal drops by.

Roy’s seen plenty of bras before in movies, the lingerie store in the mall, or when it peeks from underneath a woman’s shirt while she’s leaning a little too forward. It feels wrong to put it on when he doesn’t exactly have a chest to hold up inside the flimsy thing so he can draw the line in the sand here. _No harm, no foul. It’s fine, not like Ollie will notice anyway._ But when he pulls the dress up to his chest and slots his arms into place, the fabric of the costume rubs uncomfortably against his nipples, scratching his chest in a way that can’t be ignored. Roy glares at the bra.

“You caused this,” he mutters to the emptiness of the room, pulling his arms out and looking over how to put the top on. There’s no clasp, just lace and holes. He pulls it gently over his head to avoid messing with the wig and tries again. It’s only mildly better, albeit a slight tingle strikes him when the dress closes snug across his back. It’s tight and he realizes now that he’s glad he didn’t force wearing his boxers into the stockings. The less idiotic he can make himself out to be while in this getup, the better. Ollie might even take this type of initiative as reason enough to bring him on the serious missions and stop treating him like a little kid.

* * *

Roy has regrets on his gong-ho insistence on coming about three hours into the Charity event. Pretending to be someone’s estranged, shy niece is boring as hell and his only saving grace is being able to scarf down as many shrimp from the buffet without anyone the wiser. He hasn’t seen sight or hair of Ollie—who he guess is probably making moves on an old lady wearing too much perfume and make up. Roy bits his tongue, distracted by the bitter thought as he mills around the buffet table for something else to soothe the pain in his mouth. He sees the champagne flute pyramid and looks around to see if anyone's watching before he swipes two glasses. He chugs down the first one before his courage can escape and though the taste is different from beer it's not too bad. He nurses the second, wanting to examine the alcohol content and see if he can get drunk.

There’s a firm hand on his shoulder that scares the shit out of him as he shotguns the glass, batting wide doe eyes in the hope of coming off as a sincerely apologetical little girl while he turns to find the culprit. Ollie has a wolfish grin on his face that Roy would love to punch right now but he can’t act on it dressed like this. It would risk the mission and his chances of proving useful so he smiles as sweet as teeth rotting candy and hugs the old man’s waist.

“Find anything yet?” Roy whispers into the smooth fabric of Ollie’s tailored jacket, glancing up at his mentor expectantly. To an outsider it would seem like a girl happy to be with her Uncle. A success in Roy’s book especially when he notices the twitch in Ollie’s eyebrow. He’s probably still not used to seeing Roy like this.

“Dance with me,” Ollie offers his hand instead of an answer and Roy grimaces at the thought. He’s still growing but he’s nowhere near as tall as Ollie. He’s almost certain it would be awkward for them both but he takes the old man’s hand anyway. Ollie takes Roy out to the dance floor and it feels like everyone’s eyes are on him. His dress blooms as Ollie twirls him around in circles, the fabric coming to life as they give it movement. Roy’s head is practically at Ollie’s chest so there’s no subtle way to whisper like this but the redhead is almost certain Ollie chose this so they could speak between the loud music without being overheard. Just as Roy awkwardly sashays into the beat, Ollie turns them once more and lifts Roy up into his arms. The young hero bleats an undignified squawk, resisting Ollie until an arm cradles under his legs.

“I’m not a child!” Roy insists as he punches Ollie’s shoulder. He totally deserves it.

“Don’t be mad! This was the easiest way to talk to you,” Ollie laughs, entirely too amused with himself as the music slows and he begins to sway. Roy glares, not buying his mentor’s excuse at all as he rests his weight into his arms. 

“You’re being stupid but whatever. What did you find?” He huffs, leaning in close so that his ear is near Ollie’s mouth. Each breath Ollie takes has Roy steeling his nerves as they dance cheek to cheek, slowly moving to the song across the dance floor and embracing much like family. A weird sensation settles in his gut as Roy listens to Ollie’s information, distracted by the closeness yet unable to tear himself away. Selfishly, Roy knows he shouldn’t entertain the old man. But a part of him wants to indulge the oddness of it, their closeness that Roy couldn’t have before. He wants to sink into the warmth of Ollie’s arms and let it wash over him. Roy isn’t exactly pouting when he catches sight of the old ladies watching them and fawning over the scene. He should have known this was just some way to get into their pants but he lets himself enjoy it a little bit longer. The strangeness in his gut moves to take over his chest and Roy tunes everything else out as he tries to figure out the name for what he’s feeling.

* * *

When they crash into the penthouse, Ollie is drunk. But so is Roy because he managed to slip a few more glasses of champagne before they left. Which was a lot of fun before Roy realized his limbs felt like jelly and he can’t form any thoughts longer than a couple of seconds. He’s sluggish, stumbling and giggling through the hallway before finding the living room to toe off his heels. He face plants into the leather couch, sighing blissfully with relief as his body just settles on the fabric. Roy gives a weak attempt at his zipper on the back of his neck to escape his frilly prison but gives up when his arm muscles get tired. His hand flops over the side of the couch and he turns to watch Ollie’s legs pass by his face just as the old man comes around the couch before sitting in the free space near Roy’s head.

“Need help there, kiddo?” Ollie sounds amused and Roy twists a little bit until his head is in his mentor’s lap. He shakes the universal sign for No in reply, just wanting to sleep here. The wig suddenly lopsided from the movement as it slides on his head and he could care less because his stomach is full of the bubblies. Roy groans when he feels a heavy hand thread through the fake hair and he bats at the older hero’s leg just to get him to stop moving.

“I’m just taking it off!” Ollie laughs fingering at the hemline of the wig before fully pulling it off Roy’s skull. The cap rolls with the fake hair and Roy grumbles as the air hits his scalp. There is relief when the tension leaves him, his whole mind drifting as his skin pulses from the previous pressure. The hand returns and Roy allows it only because it feels nice. Thick, calloused fingers run across the back of his head, massaging his scalp and start to make a mess of his hair as the young hero swallows down the growing lump in his throat. Roy feels that weird sensation again from earlier, his mind slowly trying to wrap around it. It starts low in the pit of his stomach and like a clawed hand, it grabs hold of his heart, causing his chest to feel tight. He wheezes a bit, shifting uncomfortably and wiggling to try and free himself again. _It’s gotta be the dress,_ he reasons, just as Roy starts struggling to move again. His hand grabs at Ollie’s thigh as Roy tries to wrestle with his noodle limbs to help him sit up.

“Are you sleeping?” He accuses, catching Ollie with his head thrown back against the couch cushion, legs spread and posture slumped.

“Not with you yapping.” Ollie snaps, snorting when Roy pinches his chest to retaliate.

"Don't be a dick. Help me outta this before you conk out." Roy climbs onto Ollie's lap, ignorant of the implications as he sways on his perch, waiting for his body to become free of the tight fabric. He can do it himself, obviously, but Roy's being lazy and every time he invades Ollie's space, the unnamed feeling in his chest starts to loosen and flutter in a pleasant way. Ollie’s hands prod his sides, blindly searching and tickling him just a bit as the older man messes around. Roy squirms, smacking Ollie’s knee before the zipper is tugged and the tight top frees his small chest. Roy sighs, shuddering for a moment as the hand goes lower until the fabric of the zipper stops. The frilly top slips from his shoulders and Roy forgets where he is when Ollie presses a hot hand against the back of his spine, fingertips pressing against the lace of Roy’s bralette.

“Roy..what the hell are you wearing?” Ollie breathes, his voice quiet as he pushes the dress down to his sidekick’s waist to expose and see more of the questionable fabric. Roy forgot for a second who he was, what they’d been doing and why. His mind can only focus on one thing at a time right now and it is currently racing a mile a minute zeroing in on the way Ollie’s fingers graze against his skin.

“Uhm,” his mouth feels dry and he can’t even form the right words because how did Roy blank on such an important piece of information? Alcohol is dangerous, that’s for sure. He doesn’t know if he’ll ever get drunk again, if it means saving himself from this excruciating type of embarrassment. “The costume you bought?”

“No..kid. Roy. This,” Ollie hesitates and he seems to think better on his next choice of words because he’s scoping Roy up from underneath his arms and turning him around as if he were some life sized doll. If Roy’s face wasn’t already flushed pink, it is now as he instinctively covers up his chest with his arms. “Seriously. Where’s this from? I won’t get mad.”

“I’m serious! It came with the outfit! I wasn’t going to be stupid and wear my guy shit underneath that frilly thing. Besides, you didn’t know? Or bother to check what else came with it first?” Roy is trying to defend himself but for what, he doesn’t know. Ollie is the idiot who bought it. Did it make him even more stupid to wear the whole getup? Should he have thrown a fit instead? Roy shakes his head at the thought, hyper aware of Ollie’s hands on his arms and the way his mentor pointedly tries not to let his sight drift from Roy’s face. Heat blooms in his chest, making his soft freckled skin turn pink from his neck to his ears as Roy swallows around a foreign reaction.

“Wh—what? No! No, of course I didn’t know! What do you think I am?” Ollie’s voice is incredulous, staring with wide horror at the sobering thought that his sidekick thought he would do something like this. Ollie would never, or at least out loud admit to anything unsavory. It hadn’t even crossed his mind before now. Yet he couldn’t stop himself from staring.

Roy likes this. He likes watching Ollie squirm and it’s in no way innocent. The young boy keeps his arms crossed, set to come off as upset despite how much fun he is having with all of this. Ollie is watching him, but Roy’s watching Ollie too. Waiting for when he’s gone too far, pushed too much. “A deviant.”

It takes Ollie a whole minute for the word to process in his mind. To read Roy’s facial expression and gauge the seriousness of their conversation. While it may have started defensively, now, all that's here is Roy teasing Ollie for freaking out like some idiot. Ollie doesn’t take kindly to it at all. “Why, you little _shit_!” He mutters, hands reaching out immediately to Roy’s sides and beginning to tickle him like crazy. Roy screams, legs caught in the lower half of the dress, effectively trapping him and keeping the young hero from kicking out and escaping. Roy wrestles with Ollie's arms but his mentor is so much stronger than he is. He squirms, trying to bite Ollie's arms and hands as he laughs, managing to shove a hand at Ollie's chin. Roy pushes at Ollie's face as far as his short arm will go, begging as he nearly falls off Ollie's lap.

"Stop! Stop stop!!!" Roy pushes harder than he means to and for a split second he thinks he really will fall but Ollie catches him by his waist. Roy was so distracted by the tickling he didn't realize what it felt like to have Ollie touching his bare flesh. The hands on his waist feel different from the prodding fingers trying to get him to die of laughter. Roy shifts, suddenly aware of the silence between them as he stares at Ollie's expression.

The old man is staring again and all Roy can think of is the need to _feel_ more of it. He wants the hunger, Ollie's attention only on him and no one else. Blame it on drunken stupidity but when Roy leans forward, Ollie's grip tightens and on instinct Roy stops. There is only their breaths keeping them apart, the heavy smell of alcohol passing back and forth between them until Ollie murmurs, "let's go to bed..getting late and I'm sleepy."

Roy nods, unable to put a voice to the feelings in his heart. "Lemme get changed…" he shuffles to get up but Ollie stops him. Roy holds his breath, watching Ollie's hand caress his stomach before it sinks to pull at the edges of the costumed dress. Roy has never felt his heart pound so loudly in his ears and by the time his mind is screaming for him to do _something,_ the dress is off his body. Stocking clad thighs frame Ollie's lap and Roy is searching for answers in all the wrong places. He doesn't care one bit.

"Or not..ya know. Can't get mad at me for telling the truth..you're a giant perv." Roy whispers, wrapping his arms around his mentor's neck. Ollie nods like he's in a trance, not moving until Roy's secured in his arms. The young hero definitely doesn't want to admit he enjoys being carried, let alone the fact that Ollie's hands were right on his thighs and hips. Roy doesn't protest when they make it to Ollie's room and he doesn't stop Ollie from pulling him close to his warm body underneath the covers. Roy falls asleep with heavy hands on his skin and a growing heat he's realizing is desire. Hoping beyond reason that come morning Ollie won't change his mind about this new development.


End file.
